Synthesis
In a 500ml three-necked flask equipped with a stirrer, dropping funnel and thermometer, add 140ml formic acid and 56g urea-peroxide adduct, stir and dissolve. 28 g (0.17 mol) of 2-hexylcyclopentanone was added dropwise at room temperature, and the dropwise addition was completed in about 1 hour. 168 ml of water was added, and the layers were stirred and separated. The aqueous layer was extracted three times with 28 ml of toluene, and the organic Chemicalbook layers were combined. The toluene in the organic layer was distilled off under reduced pressure, and the temperature was controlled not to exceed 70° C. The residue was the crude product of butyl-undecalactone with a purity of 85% and a yield of 96%. The crude product was distilled with a vacuum thin film distillation device, at 128° C/1.4 kPa, and the distilled product was butyl-undecalactone, purity 98% ,yield 84%.
Description
Undecanolactone has a sweet, fruity, milky, creamy, buttery, estery, waxy, coconut aroma and taste. It is the key ingredient for the special flavor of natural cream and can be used for flavoring soft drinks, candy, margarine, ice cream, cold and baked goods, etc.
Chemical Properties
Δ-Undecalactone has a creamy, peach-like aroma.
Chemical Properties
Colorless to light-yellow liquid; peachlike
odor. Soluble in 4–5 volumes of 60% alcohol; soluble
in benzyl alcohol, benzyl benzoate, and most fixed
oils. Combustible.
Occurrence
Reported found in coconut flavor, melon, blackberry, blueberry, heated butter, milk, milk powder, cream,
coconut meat and starfruit.
Uses
Perfumery, flavoring agent.
Uses
Undecanoic δ-lactone has been used as substrate to investigate the activities of stimulated and nonstimulated human serum paraoxonase (PON1) samples.
Preparation
By intramolecular Cannizzaro-type rearrangement of 2-hexylglutaraldehyde.
Definition
ChEBI: 6-Hexyltetrahydro-2H-pyran-2-one is a delta-lactone.
Aroma threshold values
Detection: 150 ppb
Taste threshold values
Taste characteristics at 10 ppm: creamy, coconut, milky, creamy, lactonic and butter fat with a waxy, fruity
nuance.
General Description
Undecanoic δ-lactone has been found to be best substarte for good substrates for lactonase from
Sulfolobus islandicus (
SisLac).
Biochem/physiol Actions
Taste at 10 ppm
